Hydrogen chloride-ethyl acetate → 2-chloro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]isonicotinic acid hydrochloride

HRID 1691737Notes

Reaction equation

HRID 1691737 reaction equation
C(OC([N:8]([CH2:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:29]=[C:30]([CH:34]=[C:35]([Cl:37])[N:36]=2)[C:31]([OH:33])=[O:32])[CH2:24][CH:23]1[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.Cl.C(OCC)(=O)C>O1CCOCC1>[ClH:37].[Cl:37][C:35]1[CH:34]=[C:30]([CH:29]=[C:28]([N:25]2[CH2:26][CH2:27][CH:22]([CH2:21][NH:8][C@@H:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[CH3:10])[CH:23]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:24]2)[N:36]=1)[C:31]([OH:33])=[O:32]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 866387012-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-6-chloroisonicotinic acid

Product 1

HCID 866387022-chloro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]isonicotinic acid hydrochlorideYield 95.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 68 mg of 2-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-6-chloroisonicotinic acid in 1.0 mL of 1,4-dioxane was added 1.00 mL of a 4 M hydrogen chloride/ethyl acetate solution at room temperature, followed by stirring for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was washed with diisopropylether, and dried under reduced pressure to obtain 29 mg of 2-chloro-6-[4-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]isonicotinic acid hydrochloride as a pale yellow solid.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. washThe residue was washed with diisopropylether
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-2f4d24f0c8d549ad95750dfa0a2f0eb0
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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